EP0874870B1 - Verfahren zur herstellung von polyglycol(meth)acrylaten - Google Patents

Verfahren zur herstellung von polyglycol(meth)acrylaten Download PDF

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Publication number
EP0874870B1
EP0874870B1 EP97900971A EP97900971A EP0874870B1 EP 0874870 B1 EP0874870 B1 EP 0874870B1 EP 97900971 A EP97900971 A EP 97900971A EP 97900971 A EP97900971 A EP 97900971A EP 0874870 B1 EP0874870 B1 EP 0874870B1
Authority
EP
European Patent Office
Prior art keywords
process according
transesterification
meth
denotes
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP97900971A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0874870A1 (de
Inventor
Joachim Knebel
Werner Spalt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Roehm GmbH Darmstadt
Original Assignee
Roehm GmbH Darmstadt
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Roehm GmbH Darmstadt filed Critical Roehm GmbH Darmstadt
Publication of EP0874870A1 publication Critical patent/EP0874870A1/de
Application granted granted Critical
Publication of EP0874870B1 publication Critical patent/EP0874870B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/54—Acrylic acid esters; Methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78—Preparation processes
    • C08G63/82—Preparation processes characterised by the catalyst used
    • C08G63/83—Alkali metals, alkaline earth metals, beryllium, magnesium, copper, silver, gold, zinc, cadmium, mercury, manganese, or compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/005—Stabilisers against oxidation, heat, light, ozone

Definitions

  • the invention relates to a process for the preparation of Alkoxypolyglycol (meth) acrylates by base-catalyzed transesterification, wherein as catalysts, a mixture of lithium chloride and Calcium hydroxide or calcium hydroxide is used alone.
  • acrylic esters include those with alkoxy polyglycols.
  • the amounts are preferably in the range of 1 to 2 times the amount of catalyst used.
  • the transesterification reaction preferably takes place within a total reaction time from approx. 4 - 5 hours and at a sump temperature in the range> 100 ° C and ⁇ 120 ° C, for example ⁇ 105 ° C, especially at 110 - 118 ° C. instead of.
  • the substances are usually obtained a slightly yellowish, viscous Liquid, which at room temperature to a white, waxy mass solidifies. For example, it is mixed with water - possibly after one further filtration, a nearly colorless, clear ester of formula I obtained.
  • the alcoholysis is in 5.75 h at bottom temperatures of 109 - 114 ° C. carried out. After the reaction is cooled to 45 ° C and added to the Batch with 64.7 g Tonsil L80 FF (Südchemie). After 10 min. Stirring is the reaction mixture with 5 kg of MMA and added with the addition of 130 g Diatomaceous earth Seitz-Super (Seitz company) pressure-filtered at the same temperature. The Filtrate is mixed with 19 kg of methyl methacrylate gives 30 kg of a 25th % solution of the methacrylic ester of Lutensol® AT 25 with a Color number according to APHA of 14 and a hydroxyl number ⁇ 0.1.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
EP97900971A 1996-01-20 1997-01-09 Verfahren zur herstellung von polyglycol(meth)acrylaten Expired - Lifetime EP0874870B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19602035 1996-01-20
DE19602035A DE19602035C2 (de) 1996-01-20 1996-01-20 Verfahren zur Herstellung von Alkoxypolyglycol(meth)acrylaten
PCT/EP1997/000056 WO1997026293A1 (de) 1996-01-20 1997-01-09 Verfahren zur herstellung von polyglycol(meth)acrylaten

Publications (2)

Publication Number Publication Date
EP0874870A1 EP0874870A1 (de) 1998-11-04
EP0874870B1 true EP0874870B1 (de) 2003-03-26

Family

ID=7783282

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97900971A Expired - Lifetime EP0874870B1 (de) 1996-01-20 1997-01-09 Verfahren zur herstellung von polyglycol(meth)acrylaten

Country Status (9)

Country Link
US (1) US6040473A (zh)
EP (1) EP0874870B1 (zh)
JP (1) JP4017668B2 (zh)
KR (1) KR100468270B1 (zh)
AT (1) ATE235528T1 (zh)
CA (1) CA2243514C (zh)
DE (2) DE19602035C2 (zh)
TW (1) TW363965B (zh)
WO (1) WO1997026293A1 (zh)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10354652A1 (de) * 2003-11-22 2005-07-07 Clariant Gmbh Verfahren zur Veresterung von Alkoholen mit olefinisch ungesättigten Carbonsäuren

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU743962B2 (en) * 1997-08-29 2002-02-14 Rohm And Haas Company Transesterification process
US6140444A (en) * 1999-01-19 2000-10-31 Loctite Corporation Catalyst system, process, and silicone compositions
CN1169853C (zh) * 1999-08-23 2004-10-06 花王株式会社 (甲基)丙烯酸系聚合物的制造方法
JP4066126B2 (ja) * 2000-12-06 2008-03-26 株式会社日本触媒 ポリアルキレングリコール系単量体の貯蔵及び／又は移送方法
DE10063511A1 (de) 2000-12-20 2002-06-27 Basf Ag Verfahren zur Herstellung von Alkylpolyalkylenglykolestern monoethylenisch ungesättigter Carbonsäuren
DE10106642A1 (de) * 2001-02-12 2002-08-22 Roehm Gmbh Verfahren zur Herstellung von (Meth)acrylsäureestern durch Umesterung in Gegenwart von Alkalimetallcyanat enthaltenden Mischkatalysatoren
JP4826026B2 (ja) * 2001-05-18 2011-11-30 日立化成工業株式会社 （メタ）アクリル酸エステルの製造法
JP2006182606A (ja) * 2004-12-28 2006-07-13 Miyoshi Oil & Fat Co Ltd セメント混和剤及びセメント組成物
CN101088990B (zh) * 2006-06-13 2011-08-03 罗门哈斯公司 用来制备(甲基)丙烯酸酯单体的酯交换法
WO2008013551A1 (en) 2006-07-23 2008-01-31 Iowa State University Research Foundation, Inc. New composite-based catalysts for biodiesel production
US7906665B2 (en) 2007-10-30 2011-03-15 Iowa State University Research Foundation, Inc. Solid catalyst system for biodiesel production
FR2924114A1 (fr) * 2007-11-27 2009-05-29 Arkema France Procede de synthese de (meth)acrylates d'alcoxypolyalkylene glycols par transesterification
DE102009002632A1 (de) * 2009-04-24 2010-10-28 Basf Se Verfahren zur Herstellung von (Meth)acrylsäureestern von Polyalkoxylgruppen enthaltenden Alkoholen
JP6173308B2 (ja) * 2011-07-06 2017-08-02 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ （メタ）アクリル酸エステルの製造方法
EP2716680A1 (de) 2012-10-04 2014-04-09 Basf Se Fluorierte polymerisierbare Verbindung
DE102014202963A1 (de) 2014-02-18 2015-08-20 Basf Se Verfahren zur Herstellung von (Meth)acrylsäureestern von Polyalkoxygruppen enthaltenden Alkoholen
CN112004849A (zh) * 2018-05-31 2020-11-27 Sika技术股份公司 用于制备明确限定的梳形聚合物的方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3423443A1 (de) * 1984-06-26 1986-01-02 Röhm GmbH, 6100 Darmstadt Verfahren zur herstellung von estern der acryl- und methacrylsaeure durch umesterung
DE3423441A1 (de) * 1984-06-26 1986-01-02 Röhm GmbH, 6100 Darmstadt Verfahren zur herstellung von estern der acryl- und methacrylsaeure durch umesterung
DE4019788A1 (de) * 1990-06-21 1992-01-02 Henkel Kgaa Verfahren zur herstellung von mehrfunktionellen (meth)acrylsaeureestern
GB9120584D0 (en) * 1991-09-27 1991-11-06 Bp Chem Int Ltd Process for the preparation of acrylic acid and methacrylic acid esters
JP3443780B2 (ja) * 1994-02-15 2003-09-08 四日市合成株式会社 フェノキシポリアルキレングリコールアクリレートの製造方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10354652A1 (de) * 2003-11-22 2005-07-07 Clariant Gmbh Verfahren zur Veresterung von Alkoholen mit olefinisch ungesättigten Carbonsäuren

Also Published As

Publication number Publication date
DE19602035C2 (de) 1998-04-02
JP2000503695A (ja) 2000-03-28
US6040473A (en) 2000-03-21
CA2243514C (en) 2005-10-18
CA2243514A1 (en) 1997-07-24
EP0874870A1 (de) 1998-11-04
DE59709633D1 (de) 2003-04-30
JP4017668B2 (ja) 2007-12-05
DE19602035A1 (de) 1997-07-24
WO1997026293A1 (de) 1997-07-24
KR19990081829A (ko) 1999-11-15
TW363965B (en) 1999-07-11
ATE235528T1 (de) 2003-04-15
KR100468270B1 (ko) 2005-07-12

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